Patent GB-797995-A (GB)
Title: Derivatives of 2:4-dicarboxyalkoxy benzamides and improvements in colour photographic development processes
IPC: C07D231/52
Filed: 1955-10-14
Abstract: The invention comprises compounds falling within the general formula: <FORM:0797995/IV (b)/1> where R represents a hydrogen atom or an alkyl group, R1 represents a hydrogen atom, a methyl group or an alkali metal atom, n represents 0 or 1 and Z represents an aromatic nucleus connected to a photographic coupling function.  Z may be a mononuclear aromatic radical such as phenyl or naphthyl which may be connected to a pryazolone radical of the formula: <FORM:0797995/IV (b)/2> wherein R2 represents an alkyl group, e.g. methyl ethyl or n-propyl, or an aromatic radical, e.g. phenyl, chlorinated or brominated phenyl or naphthyl, a phenolic radical such as hydroxyphenyl, hydroxynaphthyl and substituted derivatives thereof, or the radical of an open chain ketomethylene compound. Particularly useful compounds have the general formula: <FORM:0797995/IV (b)/3> wherein Z1 represents a radical containing a pyrazolone radical as defined under 2, a phenolic or naphtholic radical or a radical containing an open chain ketomethylene group.  The products of the invention are incorporated in photographic silver halide emulsions or colour developing compositions (see Group XX). Compounds of the first formula in which R is hydrogen, n is 0 and R1 is methyl may be prepared by condensing a compound of the formula: <FORM:0797995/IV (b)/4> with an amine of the formula Z-NH2 wherein Z has the meaning given above.  The condensation may optionally be carried out in the presence of an acid-binding agent such as an alkali metal acetate or pyridine and in the presence of an inert solvent such as anhydrous acetic acid, acetone, acetonitrile, xylene or diethyl ether.  Typical amines are described in Specifications 562,205, [Group IV], 680,474 and 680,488 and in U.S.A. Specifications 2,589,004 and 2,618,641.  In examples: 5-(2 : 4-dicarbomethoxymethoxybenzamido) - 2 - (2 : 4 - ditert. amylphenoxy) benzamido - 2 : 4 - dichloro3 - methyl phenol is prepared by reacting 6-[5 - amino - 2 - 2 : 4 - ditert. amylphenoxy) benzamido] - 2 : 4 - dichloro - 3 - methylphenol and 2 : 4 - dicarbomethoxymethoxybenzoyl chloride in acetonitrile (2); 1 - phenyl - 3 - [2 - (2 : 4 - ditert.-amylphenoxy) - 5 - (2 : 4 - dicarbomethoxymethoxybenzamido) benzamido] - 5 - ayrazolone is prepared by reacting 1-phenyl-3-[2-(2 : 4 ditert. amylphenoxy) - 5 - aminobenzamido]-5-pyrazolone with 2 : 4-dicarbomethoxymethoxybenzoyl chloride in xylene (3); 1-hydroxy - N - {4 - [2 - (2 : 4 - di - tert. amylphenoxy) - 5 - (2 : 4 - dicarbomethoxymethoxy benzamido) benzamido] phenethyl} 2-naphthamide (4); and 1-(2 : 4 : 6-trichlorophenyl)-3-[3 - (2 : 4 - dicarbomethoxymethoxybenzamido]-5-pyrazolone (5) are prepared by analogous processes and a  - (4 - methoxybenzoyl) - 4 - {3-[2 : 4 - bis (carbomethoxymethoxy) benzamido] phenylcarbamylmethoxy}-acetanilide is prepared by reacting dimethyl-4-chloroformyl-1 : 3-phenylene bis-(oxyacetate) with m-nitraniline in the presence of dimethylaniline and acetone to form 2 : 4-bis-(carbomethoxymethoxy) - 31 - nitrobenzanilide, converting the latter to the corresponding amine by catalytic hydrogenation, reacting the amine with p-nitrophenoxyacetyl chloride and again reducing the product to the corresponding amine and condensing the latter with ethyl-a -(p-methoxybenzoyl) acetate in the presence of sodium acetate and xylene.  Dimethyl-4-chloroformyl-1 : 3-phenylene bis-(oxyacetate) is prepared by reacting methyl bromoacetate and b -resorcaldehyde in the presence of sodium methoxide to form 2 : 4-bis-(carbomethoxymethoxy) benzaldehyde which is oxidized to the corresponding benzoic acid with aqueous potassium permanganate and converted to the corresponding acid chloride with thionyl chloride. Other suitable acid chlorides for use as starting materials may be obtained when the method bromoacetate is replaced by methyl b -bromopropionate or methyl a -bromopropionate to give dimethyl-4-chloroformyl 1 : 3-phenylene bis (b -oxypropionate and 1 : 3 - phenylene bis - (oxy - propionate) respectively. 6-[5-amino-2-(2 : 4-ditert. amylphenoxy) benzamido]-2 : 4-dichloro-3-methylphenol is prepared by condensing 4-amino-2 : 6 - dichloro - m - cresol with 2 - (21 : 41 - ditertamylphenoxy) - 5 - nitrobenzoylchloride and reducing the nitro group in the product.  Specifications 737,103 and 758,165 also are referred to.